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Chemical Structure| 7283-96-7 Chemical Structure| 7283-96-7
Chemical Structure| 7283-96-7

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Synonyms: 5-Chloro-2-thiophenecarboxaldehyde

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Product Details of 2-Chloro-5-thiophenecarboxaldehyde

CAS No. :7283-96-7
Formula : C5H3ClOS
M.W : 146.59
SMILES Code : O=CC1=CC=C(Cl)S1
Synonyms :
5-Chloro-2-thiophenecarboxaldehyde
MDL No. :MFCD00047090
InChI Key :VWYFITBWBRVBSW-UHFFFAOYSA-N
Pubchem ID :81700

Safety of 2-Chloro-5-thiophenecarboxaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332
Precautionary Statements:P280

Application In Synthesis of 2-Chloro-5-thiophenecarboxaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 7283-96-7 ]

[ 7283-96-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 7283-96-7 ]
  • [ 612845-44-0 ]
  • 5-(6-ethoxypyridin-3-yl)-thiophene-2-carbaldehyde [ No CAS ]
  • 2
  • [ 7283-96-7 ]
  • [ 76350-90-8 ]
  • C19H16O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.039 g With bis(eta3-allyl-mu-chloropalladium(II)); di-tert-butyl (2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; caesium carbonate; In toluene;Inert atmosphere; In a 8 mL clear vial, (2-methyl-[l,l'-biphenyl]-3-yl)methanol (50 mg, 0.252 mmol), cesium carbonate (123 mg, 0.378 mmol), 2-(Di-t-butylphosphino)-3-methoxy-6- methyl-2'-4'-6'-tri-i-propyl-l, -biphenyl (7.09 mg, 0.015 mmol), 4A molecular sieves(50mg) and toluene (0.4 mL) were combined. The reaction mixture was degassed with argon gas. 5-chlorothiophene-2-carbaldehyde (55.5 mg, 0.378 mmol, Cole, Andrew G.; Letourneau, Jeffrey John; Ho, Koc-Kan WO 2010059922 Al) and allylpalladium(ii) chloride dimer (2.77 mg, 7.57 muiotaetaomicron) were added. Then reaction mixture was heated at 90C for 24hrs. The reaction mixture was diluted with ethylacetate, filtered through celite and concentrated. The residue was purified using a gradient of 0 to 15% ethylacetate inpetroleum ether on a 4 gm silica gel column. The fractions containing the product were combined and concentration to give the desired aldehyde (0.039g). Example 118 was prepared from this aldehyde and 2-amino ethanol according to the reductive amination conditions as described for Example 1.
  • 3
  • [ 7283-96-7 ]
  • [ 6882-68-4 ]
  • C20H25ClN2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h; General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.
  • 5
  • [ 7283-96-7 ]
  • [ 35475-03-7 ]
 

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